Acetic Anhydride → HCID 178526026, compound

HRID 358586Notes

Reaction equation

HRID 358586 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](=[O:17])[NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4]1.[C:18]([O:21]C(=O)C)(=[O:20])C.[C:25](=[O:28])([O-:27])[O-:26].[K+].[K+].[OH-].[Na+]>C(Cl)(Cl)Cl.O.C(O)=O>[C:18]([OH:21])(=[O:20])[C:25]([OH:27])=[O:28].[CH:25]([NH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9](=[O:17])[NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:5][CH2:4]1)=[O:26]

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178511256HCID 178511256, compound

Product 1

HCID 178526026HCID 178526026, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2.33 g of trans-4-aminomethyl-1-(4-pyridylcarbamoyl)cyclohexane, 15 ml of 99% formic acid and 18 ml of acetic anhydride was stirred and then an exothermic reaction occurred by 36° C. After refluxing for 10.5 hours, the resultant mixture was poured into ice-water and alkalized with potassium carbonate and an aqueous solution of concentrated sodium hydroxide. To the precipitated water substance was added chloroform. The obtained crystals were collected by filtration, washed with water and dried. The crystals were dissolved in ethanol and a solution of oxalic acid in ethanol added thereto. The precipitated crystals were collected by filtration and dried to give trans-4-formamidomethyl-1-(4-pyridylcarbamoyl)cyclohexane oxalate 1/2 hydrate, melting at 204°-207° C. with decomposition.

Workup

  1. customan exothermic reaction
  2. customoccurred by 36° C
  3. temperatureAfter refluxing for 10.5 hours
  4. filtrationThe obtained crystals were collected by filtration
  5. washwashed with water
  6. customdried
  7. dissolutionThe crystals were dissolved in ethanol
  8. additiona solution of oxalic acid in ethanol added
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-b3380e4023cc4f548555def0c84b6639
Source dataset
uspto-grants-1991_03
Patent number
US04997834

Reaction notes

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